Isobutyric Acid → HCID 131710653, compound

HRID 436272Notes

Reaction equation

[C:1](O)(=O)[CH:2]([CH3:4])[CH3:3].[OH:7][C:8](CBr)=[C:9]([N:13]1[C:16](=[O:17])[CH:15]([NH:18][C:19](=[O:43])[CH:20]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:21]([O:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:14]1[S:44][CH:45]=O)[C:10]([O-:12])=[O:11].[CH2:49](S)[CH2:50][CH3:51]>C1(C)C=CC=CC=1>[CH:24]([O:23][C:21]([CH:20]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:19]([NH:18][CH:15]1[C:16](=[O:17])[N:13]2[C:9]([C:10]([O:12][CH:1]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:2]3[CH:4]=[CH:51][CH:50]=[CH:49][CH:3]=3)=[O:11])=[C:8]([OH:7])[CH2:45][S:44][C@H:14]12)=[O:43])=[O:22])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 18 °C

Procedure

To 0.391 g. (1 mmol.) of mercuric acetate in a mixture of 15 ml. of toluene and 15 ml. of isobutyric acid are added 0.739 g. (1 mmol.) of 3-hydroxy-4 -bromo-2-[2-formylthio-4-oxo-3-(α-benzhydryloxycarbonylphenylacetamido)-1-azetidinyl]-2-butenoate, benzhydryl ester, as a neat solid. The mixture is stirred for 20 minutes at 18° C., after which time the solution becomes cloudy. n-Propyl mercaptan is added to the mixture, and the mixture then is filtered through activated charcoal and a filter aide. The resulting filtrate is evaporated, and a residue comprising benzhydryl 7-(α-benzhydryloxycarbonylphenylacetamido)-3-hydroxy-3-cephem-4-carboxylate is obtained.

Workup

filtrationthe mixture then is filtered through activated charcoal
customThe resulting filtrate is evaporated

Sources & evidence

ORD record: ord-2c6d5a9325cf4bac8e10e0496bba2fa0
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04008230

Reaction notes

Loading…